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1 y the substitution at the C3 position of the aziridine.
2 the allene to a strained bicyclic methylene aziridine.
3 e >99%) from enantiopure trans-disubstituted aziridine.
4 -98 %) and mostly >90 % optically active cis-aziridines.
5 2-azido-aminoalcohols, diaminoalcohols, and aziridines.
6 palladium-catalyzed cross-coupling of intact aziridines.
7 fied Stille conditions to afford substituted aziridines.
8 oenriched 2-arylphenethylamines from racemic aziridines.
9 ctive construction of complex trisubstituted aziridines.
10 tric inductions and higher overall yields of aziridines.
11 ylmethyl imines with diazoesters to give cis-aziridines.
12 y2) generates trans-alpha-lithiated terminal aziridines.
13 tained with both alkyl- and aryl-substituted aziridines.
14 means for the synthesis of alkyl-substituted aziridines.
15 been studied using the structurally similar aziridines.
16 nd application in dynamic systems other than aziridines.
17 xchange are described for carbon-substituted aziridines.
18 dine opening of tosyl-activated cyclopentene aziridine 2 and optical resolution of racemic 1 with 10-
20 ate and methanediphosphonate anions afforded aziridine 2-methyl diphosphates and methanediphosphonate
22 no phosphonates to cis- and trans-N-sulfinyl aziridine 2-phosphonates, respectively, with n-BuLi.
24 nique reactivity of the resulting N-acylated aziridine-2-carbonyl peptides facilitates their subseque
26 a-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles
27 sters, and unexpectedly, the N-Boc-protected aziridine-2-carboxylate 16b with a phenyl substituent in
29 d stereoselective peptide modification using aziridine-2-carboxylic acid-containing peptides is descr
30 mediated by the imino-BOROX catalyst to give aziridine-2-carboxylic esters with very high diastereo-
32 ion and afforded, upon deprotection, the N-H aziridine 24 in 18-32% overall yield for the three steps
34 y classes of nitrogen heterocycles including aziridines, 2H-azirines, pyrrolidines, and piperidines.
35 under otherwise identical conditions, vinyl aziridine 3a and aldehydes 2a-2l engage in reductive cou
36 Using enantiomeric iridium catalysts, vinyl aziridine 3a reacts with unprotected chiral 1,3-diols 1m
37 of N-(p-nitrophenylsulfonyl) protected vinyl aziridine 3a with primary alcohols 1a-1l to furnish bran
39 detritylation of 26, methylation of the N-H aziridine 56, oxidation of the sensitive cyclohexenedion
42 indole fragment, (b) formation of hexacyclic aziridine 80 from the reaction of cyanide with intermedi
43 -opening of the aziridinium ion derived from aziridine 80, and (d) base-promoted skeletal rearrangeme
51 l for the three-component reaction driven by aziridine aldehyde dimers has predictive value for diffe
52 syn-stereoselectivity from readily available aziridine aldehyde dimers in the Petasis borono-Mannich
53 he multicomponent conversion of amino acids, aziridine aldehyde dimers, and isocyanides into chiral p
55 a range of functionalized isocyanides in the aziridine aldehyde-driven multicomponent synthesis of pi
56 ibitor calpastatin have motivated the use of aziridine aldehyde-mediated peptide macrocyclization tow
58 The cyclization chemistry centers on using aziridine aldehydes in a multicomponent reaction with pe
60 y, the synthesis and reactivity of methylene aziridines, allene oxides/spirodiepoxides, methylene sil
61 Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the si
63 rization of five racemic and two enantiopure aziridine analogues of PSPP and the evaluation of their
64 m the palladium(II) species bearing both the aziridine and aryl groups to form the hindered C-C bond.
66 rization of enynes, [3 + 2] cycloaddition of aziridines and alkenes, and [4 + 2] hetero-Diels-Alder c
67 he phosphine-mediated [3 + 3] annulations of aziridines and allenes are experimentally simple reactio
68 ioselective ring-opening of chiral activated aziridines and azetidines with alcohols to nonracemic be
69 ation processes, leading to the synthesis of aziridines and beta-lactams (respectively), and is sugge
72 vestigated using a variety of functionalized aziridines and phenols to determine the scope of the rea
73 of the substituent in the 3-position of the aziridine, and whether the substituent in the 3-position
74 an), which is known to carbonylate epoxides, aziridines, and beta-lactones, was used to catalyze the
75 es, which induce the direct formation of the aziridines, and stereochemistry of the olefin is retaine
76 to add to the Si-face of the imine when cis-aziridines are formed and both to add to the Re-face of
81 ormational transitions, which in the case of aziridines arise from inversion at the nitrogen center.
82 e-component coupling involving N-substituted aziridines, arynes, and water promoted by trifluoroaceti
83 reactions are the first reported examples of aziridines as reaction partners in nucleophilic phosphin
85 er formation was explored with small N-alkyl aziridines, azetidines, pyrrolidines, and piperidines.
86 rently exist: doubly-activated molecules and aziridine based molecules, each of which employs a diffe
93 n rates of cyclophellitol and cyclophellitol aziridine-both covalent retaining beta-glucosidase inhib
94 of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohol
95 CH(2)OH/CH(3)CN desilylated a simple N-TBDPS aziridine but caused nucleophilic cleavage at C(1) as we
96 Selective labeling with fluorescent beta-aziridine but not beta-epoxide ABPs identifies the acid/
97 onfiguration at the terminal position of the aziridine by way of aziridine ring opening by Ni (invers
99 ohydrins were converted to the corresponding aziridines by primary-selective silylations of four azid
100 st accelerates the ring opening of aliphatic aziridines by trimethylsilylazide, inducing nucleophilic
101 that heterolysis at C(10) is faster than at aziridine C(1), in contrast to the behavior of typical a
103 If necessary, the N-4-nosyl Hough-Richardson aziridine can be isolated by filtration in a very good y
107 nation reaction of nonactivated alkynes with aziridines, catalyzed by Lewis or Bronsted acids, to for
111 n deployed to construct the optically active aziridine-containing fragment that is joined to the arom
115 ctive strategies for ring-opening of the new aziridines, deprotection of the Ts group, and subsequent
116 re alpha-acyl-beta-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)(2) + 1,10
117 philic ring-opening reactions of N-activated aziridine derivatives with thiols, beta-thioglycosyl thi
118 repared by iterative opening of epoxides and aziridines derived from homochiral cyclohexadiene cis-di
119 expansion of vinyloxiranes, -thiiranes, and -aziridines described in the literature from 1964 to 2013
120 ridine substitution patterns show that alkyl aziridines display similar reactivity to alkynyl aziridi
121 thesis of such molecules that is amenable to aziridine diversification as well as elaboration of the
122 ubstituent groups on the biologically active aziridine do not function as TbNTR or TbCPR-activated pr
125 high asymmetric inductions as seen with cis-aziridines, enabling the development of an unprecedented
127 nd to react at accelerated rates relative to aziridine exclusively by means of the a Menshutkin-type
130 lyzed SN2-type ring-opening of the activated aziridine followed by a concomitant 5-exo-dig cyclizatio
131 alkylation of 2-vinylindoles with activated aziridines followed by an intramolecular aza-Michael rea
133 rmation of gram quantities of a key tricylic aziridine from a challenging photochemical cascade react
135 direct synthesis of N-phosphorus-substituted aziridines from alkenes with dinitrogen as the byproduct
136 ubstituted imines, the optical purity of the aziridines from all of the imine substrates could be enh
138 oselective synthesis of trisubstituted vinyl aziridines from these chiral sulfinamides, simply by cha
140 ed aryl bromides and tertiary organometallic aziridines, generated from sulfinylaziridines by sulfiny
141 idines display similar reactivity to alkynyl aziridines, giving insight into mechanistic possibilitie
142 or the modified Wenker cyclization to afford aziridines has been achieved using biphasic conditions f
145 A series of novel, highly substituted N-PMP aziridines have been accessed in high yields by palladiu
147 nd nitrogen in the formation of oxiranes and aziridines; however, such reactivity is not known betwee
149 ehydes were examined and found to give trans-aziridines in 60-88% yield with 60-98% ee and trans/cis
150 h aryl aldehydes were screened to give trans-aziridines in 73-90% yield with 82-99% ee and trans/cis
152 MEDAM imines can be deprotected to give N-H aziridines in all cases except for some electron-rich ar
153 uents leads to the quantitative formation of aziridines in clean solid-to-solid reactions despite ver
154 selective formation of either functionalized aziridines in dimethylformamide (through direct bromide
158 c carbamates into [4.1.0]-carbamate-tethered aziridines in good yields and with ee values of up to 92
161 forming the desired N-phosphorus-substituted aziridines in moderate to high yields and good enantiose
164 the copolymerization reaction involves first aziridine insertion into the cobalt-acyl bond, rate dete
166 yridinium perchlorate to generate a bicyclic-aziridine intermediate, which is transformed under aziri
167 nolithium-mediated conversion of beta-alkoxy aziridines into substituted allylic sulfonamides, use of
168 N-bound phenyl rings of amines, imines, and aziridine is achieved in the presence of H(2) and B(C(6)
175 ] with Me3SiCl releases the N-functionalized aziridine Me3SiN(CH2CHPh) while simultaneously generatin
177 g HSQC NMR peaks were identified in the (13C)aziridine-modified enzyme, corresponding to detection of
181 h a N-tosyl group, rendering these alpha-CF3-aziridines much more susceptible to nucleophilic ring op
184 re the development of a new synthesis of the aziridine necessary for the aziridine--pi-nucleophile cy
186 to serve as protecting groups for the labile aziridine nitrogen found within the highly sensitive azi
189 bstrate established that ring opening of the aziridine occurs with inversion of stereochemistry.
191 ped a short and practical synthesis of 1 via aziridine opening of tosyl-activated cyclopentene azirid
192 trideoxy-L-hex-2-enopyranosides, followed by aziridine opening, leads to 3-amino-3-N-,4-O-carbonyl-2,
197 tion, the effect of fluorine substitution at aziridine positions other than nitrogen was studied.
198 Compound A (CpdA) is a stable analogue of an aziridine precursor from the African shrub Salsola tuber
203 s were utilized to afford the functionalized aziridine products as single diastereoisomers with reten
204 e of regio- and enantiocontrol to afford the aziridine products in good to excellent yields in highly
205 strated through derivatization of the chiral aziridine products to obtain a diverse array of function
209 unique strain and structure of the methylene aziridine promotes a ring-opening/ring-closing cascade t
213 rine substitution at the carbon positions of aziridine results in profound enhancements of the rate o
214 nd carbenes with strained bicyclic methylene aziridines results in a formal [3+1] ring expansion to y
215 ladium(0) on the less-hindered carbon of the aziridine ring and that alkene insertion occurs in a syn
216 in DMA led to regioselective opening of the aziridine ring at C2 to give the corresponding bicyclic
217 p-TsOH resulted in exclusive opening of the aziridine ring at the most substituted position affordin
219 tions of these genes, a possible pathway for aziridine ring formation in the azecimicins can now be p
220 odular one-pot, sequential protocol using an aziridine ring opening and intramolecular nucleophilic a
221 terminal position of the aziridine by way of aziridine ring opening by Ni (inversion), transmetalatio
222 kylation to effect regio- and stereospecific aziridine ring opening by oxygen, halogen, sulfur, and n
223 ine intermediate, which is transformed under aziridine ring opening conditions to the key intermediat
225 investigation of a regio- and stereospecific aziridine ring opening reaction presents new synthetic t
226 mpounds to give products derived from either aziridine ring opening, interaction with the cyano group
228 ereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidoc
229 or nucleophile-dependent ring-opening of the aziridine ring yields functionalized 1,2- and 1,3-diamin
230 oped by utilizing a newly discovered ethynyl aziridine ring-opening reaction in a longest linear sequ
233 new flow reaction could be combined with an aziridine-ring-opening reaction to give highly functiona
234 ks for tripeptide controls, a small molecule aziridine self-polymer mimetic, and a cysteine-minus con
235 s removal of the noncovalently protein-bound aziridine self-polymer using a novel chelating dialysis
238 ctural features such as the nature of the C2 aziridine substituent and the nature of the electrophile
242 l aldehyde gave a 71% yield and 95% ee of an aziridine that was found to be the cis- and not the tran
244 thetically exploited oxiranes and thiiranes, aziridines that lack electron-withdrawing substituents,
245 ds contain two electronically differentiated aziridines that undergo highly regioselective ring openi
246 of (R)-beta(3)-DOPA and L-DOPA from the same aziridine, the former by SmI2-mediated reductive opening
247 on of the nature of the N-substituent of the aziridine, the nature of the substituent in the 3-positi
249 triplet sensitizers that selectively produce aziridines through the spin-selective photogeneration of
250 gle catalyst transforms a racemic mixture of aziridines to a pair of regioisomeric products, each in
252 doalanines is prone to rearrangement, via an aziridine, to give predominantly trityl-protected alpha-
253 e we describe a new tool, methylthiocarbonyl-aziridine, to install acetyl-Lys mimics site-specificall
254 were developed for deprotection of the N-DAM-aziridines under acidic conditions without causing an ac
257 -, tri-, and tetrasubstituted olefins to N-H aziridines using O-(2,4-dinitrophenyl)hydroxylamine (DPH
259 ring opening of non-activated 2-substituted aziridines via intermediate aziridinium salts will be de
261 tions, N-o-(trifluoromethane)benzenesulfonyl aziridine was efficiently ring-opened to afford the amin
262 us reactions between the five components, an aziridine was formed in 85% yield and 98% ee and only tw
265 1-alkyl-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines was developed starting from the corresponding
266 ese newly synthesized nonactivated alpha-CF3-aziridines was evaluated by applying N-protonation or N-
269 catalyst; however, in those cases where cis-aziridines were formed, the configuration was opposite f
270 ng transfer hydrogenation conditions, the NH-aziridines were regioselectively opened to the correspon
272 this can be particularly pronounced with cis-aziridines where a nearly equal mixture of the two is ob
273 generate separable, diastereomeric bicyclic-aziridines, which are then independently transformed to
274 the observed absolute stereochemistry of the aziridines, which undergo nucleophilic ring opening to y
275 have found that N-diphenylphospinyl and N-H aziridines, while participating in the initial ring-open
276 ia in situ formed N-4-nosyl Hough-Richardson aziridine with nitrogen nucleophiles under mild conditio
277 lso been synthesized via the ring-opening of aziridines with 2-bromobenzyl alcohols and -mercaptan, r
278 gh an S(N)2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by a hithert
279 type ring opening of enantiopure N-activated aziridines with 2-bromoindoles followed by copper-cataly
280 been developed by ring-opening of activated aziridines with 2-hydroxyphenyl acrylates and 2-aminophe
283 domino ring-opening cyclization of activated aziridines with aryl and alkyl isothiocyanates has been
285 ing of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is present
286 ions involve a regiospecific ring opening of aziridines with benzimidazoles to give benzoimidazolylet
287 lyzed S(N)2-type ring opening of substituted aziridines with electron-rich arenes/heteroarenes to pro
289 -N-acyloxazolidinones to give trisubstituted aziridines with excellent diastereo- and enantioselectiv
290 synthetically useful chiral [3.1.0]-bicyclic aziridines with high diastereo- and enantioselectivity.
291 catalyzed SN2-type ring opening of activated aziridines with indoles having substitutions at 3- and o
292 eoselective deprotonation of simple terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide (L
293 ring-opening cyclization (DROC) of activated aziridines with malononitrile in excellent yield and ste
294 The intramolecular cyclization reactions of aziridines with pi-nucleophiles can be a useful route to
295 and aliphatic aldehydes both gave the trans-aziridines with the same absolute configuration with the
296 me imines with diazoacetamides to give trans-aziridines with the same high asymmetric inductions as s
297 the C-N cleavage product is observed for all aziridines with the strongly N-activating p-toluene sulf
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